Category: 6797-13-3

Synthetic Route of C9H9NO. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Site-Selective and Stereoselective C(sp3)-H Borylation of Alkyl Side Chains of 1,3-Azoles with a Silica-Supported Monophosphine-Iridium Catalyst. Author is Murakami, Ryo; Iwai, Tomohiro; Sawamura, Masaya.

Site-selective and stereoselective C(sp3)-H borylation of alkyl side chains of 1,3-azoles with bis(pinacolato)diboron was effectively catalyzed by a silica-supported monophosphine-iridium catalyst. The borylation occurred under relatively mild conditions (2 mol% Ir, 50-90°), affording the corresponding primary and secondary alkylboronates. This system was applicable to a variety of 1,3-(benzo)azoles such as thiazoles, oxazoles, and imidazoles.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some reactions of nitriles as acid anammonides》. Authors are Holljes, Edward L. Jr.; Wagner, E. C..The article about the compound:2-Ethylbenzo[d]oxazolecas:6797-13-3,SMILESS:CCC1=NC2=CC=CC=C2O1).Category: benzoxazole. Through the article, more information about this compound (cas:6797-13-3) is conveyed.

Nitriles may be considered as ammono-acid “”anhydrides”” or acid anammonides. They react with ο-C6H4(NH2)2 (I), with 1,3-diamines such as 1,8-C10H6(NH2)2 (II) and ο-H2NC6H4CONH2 (III), or with ο-HOC6H4NH2 (IV) with formation of heterocyclic ring derivatives similar to the Ladenburg type as effected by means of carboxylic acids or their anhydrides. It is found that the initial step is the addition of proton to the nitrile, forming a reactive cation: RCN+H+ ⇌ [RC:NH ⇔ RCNH]+. When I and PhCN (V) are refluxed for 24 hrs. or heated in a sealed tube at 200° for 6 hrs. no reaction takes place. When, however, I.HCl is used, 72% 2-phenylbenzimidazole (VI), m. 287-8°, is formed. In the same way the following 2-substituted benzimidazoles are prepared: H, 5.9% yield, m. 170.5°; Me, 27.3%, m. 173.6°; Et, 58.8%, m. 172°; Pr, 71%, m. 157-9°; Bu, 47.4%, m. 150°; Am, 50%, m. 162°; p-MeC6H4, 70.9%, m. 266-9°. The rate of the reaction depends upon the ratio of acid to nitrile and with a ratio of 1:1 NH4Cl is formed which also promotes the reaction. The reaction of I with nitriles proceeds as follows: I.HCl + RCN ⇌ I + RC(:NH)Cl (VII); VII + I → ο-HCl.H2NC6H4NHC(:NH)R (VIII); VIII → ο-HN.C6H4.N:CR (IX) + NH4Cl. The formation of VII is proven by the fact that when I and PhC(:NH.HBr)Br or PhC(:NPh)Cl (X) are heated to 100°, 56% or 57% VI is formed. X, b3 146°, m. 37°, is prepared in 80-90% yield according to a modified method of Wallach (Ann. 184, 79(1877)). When I and X are allowed to react for 1 hr. at below 5°, 68% N-phenyl-N’-ο-amino-phenylbenzamidine-HCl is formed which softens at 126-40° and, when heated at 200° or allowed to stand for 2 weeks at room temperature, gives quantitatively VI and PhNH2, indicating that VIII is an intermediate product. While the formation of VIII and IX takes place very rapidly, the formation of VII is the rate-determining step. When I and VII (R = Ph) are allowed to react in ligroin (70-90°), VI and PhC(:NPh)NHPh (XI) are formed. XI and I.HCl at 200° give 46% VI but in the absence of HCl no VI can be isolated. The analogy between acids, anhydrides, amidines and nitriles and their ability to form IX from I are shown in the following scheme: When 2.16 g. IV and 1.09 g. V are refluxed for 24 hrs. or heated at 200° for 9 hrs., 54% or 51% ο-O.C6H4.N:CPh (XII), m. 102.5-3.5°, is formed. When IV.HCl is used, 72% XII is obtained in 2 hrs. The following 2-substituted benzoxazoles (XIII) are prepared: Me, 33.5% yield, b12 59-60°; Et, 61.2%, b2 75-6°; Bu, 49.7%, b20 68-70°; Am, 52.6%, b2 114-14.5°; p-MeC6H4, 72%, m. 114°. 2-Furonitrile and 2,6-(MeO)2C6H3CN fail to give XIII. In this case too, the reaction is promoted by the presence of H ions. The course of the reaction is as follows: IV.HCl + RCN → IV + VII → ο-HOC6H4NHCR:NH (XIV) or ο-H2NC6H4OCR:NH (XV) + HCl, XIV or XV heated in the presence of HCl → XIII. The formation of VII is shown by the fact that when IV and X are heated up to 100°, 58% XII is formed. When IV and VII are allowed to react in CHCl3 at a low temperature, 82% of a compound, C19H16N2O.HCl, is formed from which 72% free base (XVI), pale yellow needles, m. 80-90°, (picrate, m. 134° (corrected)) is isolated by decomposition with alkali. XVI is found to be identical with XIV but it is not methylated by CH2N2, probably due to chelation of the OH group (cf. Herzig, et al., Ber. 39, 1557(1906); Monatsh. 25, 511(1904)). II.2HCl (2.31 g.) and 0.01 mol. MeCN heated in a sealed tube for 4 hrs. give 46.7% 2-methylperimidine-HCl: 2-Pr derivative is formed in 37% yield. The course of the reaction is the same as in the formation of XIII. III, when heated with Ac2O, PrCO2H or BzOH for 3 hrs. at 200° gives 36.2% 2-methyl- (XVII), m. 239-41°, 31.9% 2-propyl- (XVIII), m. 200-2°, or 18% 2-phenyl-3,4-dihydro-4-quinazolone (XIX), m. 217-19°. III.HCl and MeCN, PrCN or PhCN for 2 hrs. at 200° give 19.7% XVII, 22.6% XVIII or 18.5% XIX. III and MeCN give less than 6% XVII. The ring closure may occur through an addition product, ο-H2NOCC6H4NHC(:NH)R. It is suggested that in the formation of 2-substituted quinazolones from ο-H2NC6H4CO2H and nitriles in which the nitrile N enters into the ring, an intermediate of the structure, ο-HO2CC6H4NHCR:NH ⇌ ο-HO2CC6H4N:CRNH2 is formed instead of ο-H2NC6H4CONHCOR (cf. Bogert and Hand, Am. Chem. J. 24, 1931(1902)).

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Synthesis and characterization of amino glucose-functionalized silica-coated NiFe2O4 nanoparticles: A heterogeneous, new and magnetically separable catalyst for the solvent-free synthesis of 2,4,5-trisubstituted imidazoles, benzo[d]imidazoles, benzo[d] oxazoles and azo-linked benzo[d]oxazoles.SDS of cas: 6797-13-3.

Amino glucose-functionalized silica-coated NiFe2O4 nanoparticles (NiFe2O4@SiO2@amino glucose) were chem. synthesized and characterized by transmission electron microscope (TEM), X-ray diffraction (XRD), thermal gravimetric anal. (TGA), energy dispersive X-ray anal. (EDX), vibrating sample magnetometer (VSM), Zetasizer and Fourier transform IR spectroscopy (FT-IR) instruments. NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of 2,4,5-trisubstituted imidazoles through one-pot multicomponent condensation of benzil or benzoin, ammonium acetate with aryl aldehydes and for the synthesis of benzoxazoles using condensation reaction of 2-aminophenol with aryl aldehydes under solvent free condition. In the other study, this synthesized magnetically reusable catalyst was introduced as a new avenue for the synthesis of benzo[d]imidazoles using the reaction between aryl aldehydes and 1,2-diaminobenzene. These compounds were obtained in high yields and short reaction times. The catalyst could be easily recovered and reused for five cycles with almost consistent activity. Synthesized compounds were characterized by their phys. constant, comparison with authentic samples, FT-IR, 1H NMR, 13C NMR spectroscopy and elemental anal.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

COA of Formula: C9H9NO. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Biomimetic Synthesis of Benzimidazoles, Benzoxazoles and Benzothiazole via the Group Transfer of Tetrahydrofolate Models. Author is Wen, Xueshan; Chen, Jianxin; Zhao, Yanqin; Chang, Xingmao; Ma, Jiachun; Zheng, Wenjun.

2-Substituted benzimidazoles, benzoxazoles I [R = Et, n-Pr, i-Pr, etc.; X = NH,O], and 2-cyclohexylbenzothiazole were prepared in good yields by biomimetic reaction of o-phenylenediamine/o-aminophenol/o-aminothiophenol with imidazolium iodides as tetrahydrofolate model compounds at the oxidation level of formate. The reaction probably involved nucleophilic addition to the C=N bond at the imidazolium ring followed a 1,3-H migration at imidazolidine intermediate and a salt elimination. This biomimetic synthesis method offers advantages such as good yields of products, easy work-up, mild reaction conditions without the use of oxidants, acid, catalyst or microwave irradiation

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: 2-Ethylbenzo[d]oxazole(SMILESS: CCC1=NC2=CC=CC=C2O1,cas:6797-13-3) is researched.Recommanded Product: cis-Dichlorobis(pyridine)platinum(II). The article 《Silica-sulfuric acid catalyzed microwave-assisted synthesis of substituted benzoxazoles and their antimicrobial activity》 in relation to this compound, is published in International Research Journal of Pharmacy. Let’s take a look at the latest research on this compound (cas:6797-13-3).

Benzoxazole derivatives were designed for a study of their biol. activity, the synthesis of the target compounds was achieved by a microwave-mediated method using sulfated silica (solid acid) as catalyst and ortho esters and 2-aminophenol derivatives as starting materials and the products thus obtained were confirmed by 1H-NMR and MS. The title compounds were screened against Staphylococcus aureus, Escherichia coli, Candida albicans and Candida glabrata (yeast) and it was discovered that these compounds displayed antimicrobial activity in comparison with Trimethoprim and Miconazole.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 6797-13-3, is researched, SMILESS is CCC1=NC2=CC=CC=C2O1, Molecular C9H9NOJournal, Article, Research Support, Non-U.S. Gov’t, Journal of Organic Chemistry called Catalytic Direct α-Amination of Arylacetic Acid Synthons with Anilines, Author is Kumar, Jogendra; Suresh, Eringathodi; Bhadra, Sukalyan, the main research direction is regiospecific amination arylacetic acid synthon aniline benzazole transformation.Product Details of 6797-13-3.

A unique α-amination approach using various anilines has been developed for arylacetic acids via adaptation as benzazoles. The reaction proceeds through a single electron transfer mechanism utilizing an iron-based catalyst system to access α-(N-arylamino)acetic acid equivalent Modification of approved drugs, facile cleavage of the benzazole auxiliary, and tolerance of amide linkage forming conditions constitute the potential applicability of this strategy.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Related Products of 6797-13-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Magnetic nanoparticles-supported tungstosilicic acid: as an efficient magnetically separable solid acid for the synthesis of benzoazoles in water. Author is Khalafi-Nezhad, Ali; Panahi, Farhad; Yousefi, Reza; Sarrafi, Sina; Gholamalipour, Yasaman.

The magnetic nanoparticles-supported tungstosilicic acid (TSAMNP) was found to be a highly efficient solid acid for the synthesis of benzoazoles in water. TSAMNP catalyst was achieved by the immobilization of tungstosilicic acid [H4(W12SiO40)] species on the silica core-shell magnetic nanoparticles (Fe3O4@SiO2). A variety of aldehydes were successfully condensed with 1,2-diaminobenzene, 2-aminophenol and 2-aminothiophenol in water as a green solvent to synthesize benzoazoles in good-to-excellent yields. TSAMNP catalyst was easily separated from the reaction mixture and reused several times without any loss of efficiency.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Related Products of 6797-13-3. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Ruthenium-Catalyzed Synthesis of Benzoxazoles Using Acceptorless Dehydrogenative Coupling Reaction of Primary Alcohols with 2-Aminophenol under Heterogeneous Conditions. Author is Khalafi-Nezhad, Ali; Panahi, Farhad.

An efficient ruthenium-catalyzed acceptorless dehydrogenative coupling reaction of primary alcs. with 2-aminophenol for one-pot synthesis of benzoxazoles e. g., I, is introduced. The phosphine-functionalized magnetic nanoparticles (PFMNPs; Fe3O4@SiO2@PPh2) as a magnetic recyclable phosphorus ligand in the presence of Ru2Cl4(CO)6 was found to be an efficient heterogeneous catalytic system for promotion of the designed protocol. The reaction was carried out efficiently with a variety of substrates to give the corresponding products in moderate to good yields.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Mohammadpoor-Baltork, I.; Moghadam, M.; Tangestaninejad, S.; Mirkhani, V.; Zolfigol, M. A.; Hojati, S. F. published the article 《Silica sulfuric acid catalyzed synthesis of benzoxazoles, benzimidazoles and oxazolo[4,5-b]pyridines under heterogeneous and solvent-free conditions》. Keywords: orthoester aminophenol phenylenediamine aminopyridinol cyclization silica sulfuric acid catalyst; benzoxazole preparation orthoester aminophenol cyclization silica sulfuric acid catalyst; benzimidazole preparation orthoester phenylenediamine cyclization silica sulfuric acid catalyst; oxazolopyridine preparation orthoester aminopyridineol cyclization silica sulfuric acid catalyst.They researched the compound: 2-Ethylbenzo[d]oxazole( cas:6797-13-3 ).Synthetic Route of C9H9NO. Aromatic heterocyclic compounds can be divided into two categories: single heterocyclic and fused heterocyclic. In addition, there is a lot of other information about this compound (cas:6797-13-3) here.

A simple, rapid and efficient method for the preparation of benzoxazoles, benzimidazoles and oxazolo[4,5-b]pyridines from the reaction of orthoesters with o-aminophenols, o-phenylenediamine and 2-amino-3-hydroxypyridine in the presence of silica sulfuric acid under heterogeneous and solvent-free conditions is reported. The significant features of this method are short reaction times, high yields of the products, mild reaction conditions, solvent free reaction, cheapness, non-toxicity and reusability of the catalyst.

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem

Safety of 2-Ethylbenzo[d]oxazole. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: 2-Ethylbenzo[d]oxazole, is researched, Molecular C9H9NO, CAS is 6797-13-3, about Synergistic catalysis: highly diastereoselective benzoxazole addition to Morita-Baylis-Hillman carbonates.

An expedited method was developed for the diastereoselective synthesis of highly functionalized alkyl-azaarene systems with good yield and high diastereoselectivity (>15:1 dr). The methodol. includes a synergistic catalysis event involving organometallic (10 mol% AgOAc) activation of an alkyl azaarene and Lewis base (10 mol% DABCO, 1,4-diazabicyclo[2.2.2]octane) activation of a Morita-Baylis-Hillman carbonate. The structure and relative configuration of a representative product were confirmed by X-ray anal. The synthesis of the target compounds was achieved by a reaction of (alkyl)benzoxazole derivatives, such as 2-ethyl-6-(nitro)benzoxazole, 5-chloro-2-ethyl-6-nitrobenzoxazole, 2-(ethyl)oxazolo[5.4-b]pyridine, 4-methyl-3-nitropyridine, with Morita-Baylis-Hillman carbonates, such as β-[[(1,1-dimethylethoxy)carbonyl]oxy]-α-(methylene)benzenepropanoic acid ester derivatives

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Reference:
Benzoxazole – Wikipedia,
Benzoxazole | C7H5NO – PubChem